Acetic Anhydride → 1-Acetoxy-3-(3-methoxy-3-methylbut-1-yl)-5-methylcyclohexane

HRID 483703Notes

Reaction equation

HRID 483703 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH3:8][O:9][C:10]([CH3:22])([CH3:21])[CH2:11][CH2:12][CH:13]1[CH2:18][CH:17]([CH3:19])[CH2:16]C(O)C1.C([O-])(=O)C.[Na+]>C1(C)C=CC=CC=1>[C:5]([O:4][CH:1]1[CH2:16][CH:17]([CH3:19])[CH2:18][CH:13]([CH2:12][CH2:11][C:10]([O:9][CH3:8])([CH3:22])[CH3:21])[CH2:2]1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 147939953-(3-Methoxy-3-methylbutyl)-5-methylcyclohexanol

Product 1

HCID 147940011-Acetoxy-3-(3-methoxy-3-methylbut-1-yl)-5-methylcyclohexane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Acetic anhydride (1.4 mL, 0.014 mol), 3-(3-methoxy-3-methylbut-1-yl)-5-methylcyclohexan-1-ol (2.0 g, 0.0033 mol), toluene (3.0 mL) and sodium acetate (0.05 g) were combined and heated at reflux for 16 hours. Workup provided 1-acetoxy-3-(3-methoxy-3-methylbut-1-yl)-5-methylcyclohexane, bp0.5 175-177~-C. (1.61 g) as a mixture of diastereoisomers (ratio 92.3:3.2:4.5); NMR(CDCl3)δ 0.6(q,1H), 0.9(d,3H), 1.0-1.3(m,3H), 1.2(s,6H), 1.4-1.6(m,4H), 1.6-2.0(m,4H), 2.1(s,3H), 3.2(s,3H), 5.1(m,1H); IR(neat) 2960, 2925, 1740, 1460, 1380, 1250, 1085, 1015 cm-1 ; MS(m/e) 43, 73, 93, 108, 149, 164, 181, 241, 242.

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hours

Sources & evidence

ORD record
ord-ed43ca9bff904423bcb5cdc184debe52
Source dataset
uspto-grants-1993_07
Patent number
US05225608

Reaction notes

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